
Vacation rentals with a pool in Westhampton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westhampton
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Hamptons Oasis: pool, grill, lush landscape
Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach, walkable to downtown Westhampton.

Stylish+Cozy Hamptons Winter Getaway-5min to Beach
Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Brand new house with an all year round hot tub.
Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Beach House Feel - newly renovated backyard Oasis
You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Stunning 3 bed 2 bath home W Pool
Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Hampton's Haven
5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Peaceful Retreat in Immaculate Architect’s House
This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters

Cheerful East Hampton home with Pool
Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.
Popular amenities for Westhampton rentals with a pool
House rentals with a pool

Joyful Beach House, viewing The Great South Bay

Hampton Bays Hideaway! Hot Tub, Sauna, Beach, Pool

Hamptons Getaway/ Backyard OASIS/Monthly available

Luxury retreat w/ heated pool, steps to the Beach!

Chic Hamptons Hideaway: Beach Bungalow w/ Pool

Walker House

Hampton Bays village summer home!

Luxury modern farmhouse with heated pool & hot tub
Condo rentals with a pool

Greenport Getaway at Cliffside Condos

Beautiful condo on Long Islands Northfork

2 BR Waterfront Autumn Escape in Wine Country

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Newly Renovated Modern Townhouse w/Pool & Tennis

1856 Trading House close to water

Waterfront Summer Escape in Wine Country: 2BR
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool

East Hampton Ranch with Access to Clearwater Private Beach
Saltbox with Separate Poolhouse in Northwest Woods

Beach Barn w/ Heated Pool & Sauna - Dog Friendly
When is the best time to visit Westhampton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ2,989 | ﺩ.ﺇ2,754 | ﺩ.ﺇ2,659 | ﺩ.ﺇ2,696 | ﺩ.ﺇ3,673 | ﺩ.ﺇ3,893 | ﺩ.ﺇ4,774 | ﺩ.ﺇ4,264 | ﺩ.ﺇ3,489 | ﺩ.ﺇ3,327 | ﺩ.ﺇ3,309 | ﺩ.ﺇ3,309 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Quick stats about vacation rentals with a pool in Westhampton

Total vacation rentals
Explore 140 vacation rentals in Westhampton

Nightly prices starting at
Westhampton vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 of Westhampton vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westhampton rentals

4.9 Average rating
Westhampton stays are highly rated by guests—averaging 4.9 out of 5!
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- Yale University
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